Formaldehyde → Benzenamine, 2,6-diethyl-N-methylene-

HRID 1283715Notes

Reaction equation

HRID 1283715 reaction equation
[CH2:1]([C:3]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][CH3:11])[C:4]=1[NH2:5])[CH3:2].C=O.[CH3:14]N(C)C.CCCCCCC>O>[CH2:14]=[N:5][C:4]1[C:6]([CH2:10][CH3:11])=[CH:7][CH:8]=[CH:9][C:3]=1[CH2:1][CH3:2]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 1146TrimethylamineHCID 8900HeptaneHCID 113692,6-Diethylaniline

Product 1

HCID 93179Benzenamine, 2,6-diethyl-N-methylene-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2,6-Diethylaniline (149.2 grams; 1.0 mole), paraformaldehyde (40 grams), a 25% solution of trimethylamine (1.7 grams) and heptane were charged into a glass reaction vessel equipped with a mechanical stirrer, thermometer and reflux condenser connected to a Dean-Stark trap. The reaction mixture was heated and the water formed removed by azeotropic distillation. When no more water could be removed, the reaction mixture was stripped of solvent and distilled to yield the desired product N-methylene-2,6-diethylaniline as a colorless oil having a boiling point of 65°C.

Workup

  1. customequipped with a mechanical stirrer
  2. temperaturethermometer and reflux condenser
  3. temperatureThe reaction mixture was heated
  4. customremoved by azeotropic distillation
  5. customWhen no more water could be removed
  6. distillationdistilled

Sources & evidence

ORD record
ord-a26446e271234d7e90fffaa1f747d90e
Source dataset
uspto-grants-1976_08
Patent number
US03976471

Reaction notes

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